6-Bromoquinoline → HCID 67401202, compound

HRID 912903Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[C:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:15]([O:14][C:12]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[CH:5]3)[CH2:21][CH2:20]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of the 6-bromoquinoline (328 mg, 1.6 mmol, TCI America), 1-BOC-piperazine (340 mg, 1.8 mmol, Aldrich), tris(dibenzylideneacetone)dipalladium(0) (75 mg, 0.1 mmol, Strem), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (91 mg, 0.15 mmol, Strem) and sodium-tert-butoxide (252 mg, 2.7 mmol, Aldrich) in toluene (4 mL) was heated at 150° C. in a microwave synthesizer for 13 min. The reaction mixture was cooled to room temperature, diluted with EtOAc (5 mL) and filtered through a Celite® pad. The filtrate was concentrated in vacuo and the residue was dissolved in MeOH (4 mL) and purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as pale-yellow oil. MS (ESI, pos. ion) m/z: 314 (M+1).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a Celite® pad
concentrationThe filtrate was concentrated in vacuo
dissolutionthe residue was dissolved in MeOH (4 mL)
custompurified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

Sources & evidence

ORD record: ord-711393c4caf446b8b53a9b81dcc4bd47
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026241B2

Reaction notes

Loading…